Best Time to Visit Chicago, Illinois

The best time to visit Chicago is in the late spring months of April and May and in the autumn months of September and October. Temperatures during the spring and autumn are pleasant and mild, and there’s less rain and fewer tourists about.

Summer is peak season in Chicago, and the city swells with both locals and tourists venturing outdoors to enjoy festivals, recreational activities, and the lovely weather. Hotel rates tend to be higher during the summer, so be sure to book early!

Chicago’s notoriously bitter winters are best avoided for most travelers. If you don’t mind bundling up against the cold, though, you’ll find some great airfare and hotel deals during the winter season.

Not sure exactly when to head to the Windy City? Discover when to go with this in-depth guide to Chicago’s weather by season and month!

Weather in Chicago

By season


Spring falls between March and May in Chicago and is generally windy, cool, and rainy. Days are cloudy and chilly in March, with average temperatures being around 37°F (3°C), gradually warming up to 59°F (15°C) in May.

Frost and snowfall are still frequent in March, and in early April, it can still snow. Towards the end of April, however, things start thawing out and warming up.


It may feel slightly colder in spring due to the wind chill factor – hence Chicago’s being known as “the Windy City”—but it’s still a time of blossoming for flowering plants. Spring is the perfect time of year to hit the botanical gardens and state parks around the city. With the first warm days of April and May, there may be thunderstorms in the afternoon or the evening.


Chicago lives up to its name of the Windy City in summer when the cooler air from the lake meets the warmer air temperatures to create regular breezes. Lasting from June until August, summer is also the rainiest time of the year, with frequent thunderstorms in the afternoons and evenings.


Temperatures during the day in summer range from between 68°F and 73°F (20°C and 23°C) in June to the high 20s and low 30s in August. August often sees heat waves with high humidity levels and temperatures of around 95°F (35°C).

Despite the hot and humid weather, summer is packed with fun festivals and plenty of activities to enjoy outside, including hanging out on Chicago’s beautiful beaches. Don’t miss the free fireworks shows twice a week during the summer on Navy Pier.


For travelers, fall is one of the best times of the year to visit Chicago. In early September, the weather still has hints of summer, with warm, humid days and the odd afternoon thunderstorm.

You’ll find temperatures cooling in October, mixing gloriously mild and sunny days with some chilly nights. Early fall is still a good time to enjoy summer activities like river cruises, outdoor festivals, and outdoor dining without crowds.


Late October and early November sometimes experience an Indian summer with lovely days of around 68°F (20°C) and cold evenings with frost. By mid-November, it gets colder, and the first snowfalls begin.

Autumn is a great time of year to explore the top Chicago attractions, including the city’s museums, art galleries, and world-class restaurants. You’ll also find good deals on airfares and hotels as the summer crowd makes its way home.


Cold, cold, cold: Chicago’s winters are similar to those in Northern Europe and much like the USA’s famously-cold neighbor to the north, Canada. Skies are grey, the north wind blows in gusts, and snowfall and snowstorms are frequent.


Temperatures in December and February hang around 28°F (-2°C), while in January, the coldest month of the year, they drop to 23°F (-5°C). Cold snaps occur with temperatures dropping to 14°F (-10°C) and everything freezes over.

The freezing winter weather tends to keep visitors away and you’ll find flights and hotels with plenty of space. If you don’t mind bundling up in layers, you’ll find plenty of indoor activities to fill up your day in Chicago, from exploring museums to catching shows at theaters.

By month


January is usually the coldest month of the year in Chicago. Temperatures are generally below freezing during the day and night, and you’ll find plenty of snow around. Days are short, with only 4.5 hours of sunshine, and temperatures range between 16°F (-9°C) and 31°F (-1°C).

Montrose Harbor in January

Despite the cold weather, January is a good time to visit the city if you’re on a budget. January sees very few tourists, and hotel prices are at their lowest. Just be sure to wear plenty of layers!

Festivals & events in January

  • Chicago Polar Plunge
  • Chinese New Year Parade in Chinatown
  • Chicago International Puppet Theater Festival
  • Chicago Restaurant Week
  • The Winter Wonderfest


Chicago is still very cold in February, with temperatures below freezing and snow on the ground. Skies are grey, and days see only five hours of sunshine. Temperatures range from 20°F (-7°C) to 35 °F (1.5°C) and you won’t see many tourists around.

Chicago Theatre in February

Hotels and airfare prices are still low and there are one or two events worth braving the cold for, like Chicago Restaurant Week and Chicago Theater Week.

Festivals & events in February

  • Chicago Restaurant Week
  • Chicago Auto Show
  • Chicago Theatre Week


The freezing weather seems to break in March, however, is still very unpredictable. You might encounter lovely warm days followed by cold snaps with frost and snow. Tourism begins to pick up in March, particularly just before St. Patrick’s Day, which is a big deal in Chicago.

Plaza of the Americas in March

Temperatures during March average between 29°F (-1.5 °C) and 45°F (7°C), and days enjoy up to six hours of sunshine.

Festivals & events in March

  • Patrick’s Day Downtown Parade & River Dyeing
  • Northwest Side Irish Parade
  • Shamrock Shuffle
  • Garfield Park Conservatory Spring Flower Show
  • Brewology Beer Fest


By April, the weather in Chicago has begun to warm up considerably, and some days are bright and sunny. There’s still the chance of the odd rain shower, so it’s best to carry an umbrella with you.

Michigan Avenue in April

Spring break brings plenty of tourists to town and it’s a wonderful time to visit the city’s parks to see the spring flowers begin to blossom. Be sure to check out the tulips on Michigan Avenue.

Temperatures at night have risen above zero to around 39 °F (4 °C) and daytime temperatures are a mild 58 °F (14.5 °C).

Festivals & events in April

  • One-of-a-Kind Spring Show
  • The International Exposition of Contemporary & Modern Art (Expo Chicago)


May is one of the best months of the year to visit Chicago. Days are sunny and pleasant, with temperatures floating between 49°F (9.5°C) and 70°F (21°C). Towards the end of the month, the mercury can reach the mid-20s, making May a perfect time for getting outdoors and sightseeing.

Wrigley Field in May

It’s the perfect time to visit the city before the summer crowds arrive, and you’ll find plenty of hotel rooms and restaurant tables without having to book early.

Festivals & events in May

  • Mayfest
  • Belmont-Sheffield Music Festival
  • Mole de Mayo
  • Sueños Music Festival


Summer has arrived and temperatures are becoming milder, but June is also when the summer rains begin. Days are lovely and long with over 10 hours of sunshine a day, and temperatures range between 59°F (15°C) and 80°F (26.5°C).

John Hancock Center in June

Despite the rain, tourists begin to arrive in June, and the city starts buzzing with festivals and outdoor events. Flights and prices at the best Chicago hotels tend to rise at this time; make sure to book early to get the best deals.

Festivals & events in June

  • Old Town Art Fair
  • Wells Street Art Festival
  • Do Division Street Fest & Sidewalk Sale
  • Andersonville Midsommarfest
  • Gold Coast Art Fair
  • LGBTQ Chicago Pride Fest
  • Pride in the Park


Chicago is hot and humid in July, and it’s the busiest month for tourism. You’ll find a full calendar of festivals and events, and bars and restaurants will be jam-packed. The annual 4th of July celebration is big in Chicago, as well as fireworks shows from the Navy Pier every week.

CTA L Train in July

Temperatures are warm to hot, ranging between 65°F (18°C) to 84°F (29°C), with high levels of humidity and frequent rainfalls.

Festivals & events in July

  • NASCAR’s Chicago Street Race
  • Windy City Smokeout
  • Millennium Art Festival
  • Taste of Chicago
  • Grant Park Music Festival
  • Square Roots Festival
  • Southport Art Fair


The warm, muggy weather continues into August, and this is a fantastic time to enjoy water activities on the lake. Temperatures are similar to those in July, ranging from 65°F (18°C) to 84°F (29°C) and evenings are perfect for alfresco dining.

Navy Pier in August

August is still a busy month with loads of festivals and outdoor activities to enjoy. Don’t miss the world-renowned Lollapalooza Festival in early August.

Festivals & events in August

  • Lollapalooza Festival
  • Northalsted Market Days
  • Grant Park Music Festival
  • Chicago in Tune
  • Chicago Air and Water Show


September is one of the best months to visit the Windy City. Temperatures are still warm, the rain has eased off, and days are sunny and dry.

Chicago River in September

After Labor Day weekend, the summer crowds disperse, leaving the city fairly empty to enjoy. Bask in daytime temperatures of around 75°F (24°C), but nights are still warm enough for dining outside or a dip in your hotel pool.

Festivals & events in September

  • ARC Music Festival
  • North Coast Music Festival
  • Chicago Gourmet
  • Bike the Drive
  • Riot Fest
  • Pitchfork Music Festival
  • Hyde Park Jazz Festival


The balmy spring weather continues into October, with temperatures cooling only slightly. This month is the perfect time for exploring the city on foot or hiking in the region’s state parks.

Chicago Marathon in October

The second week of October sees the fall foliage make an appearance in beautiful hues of orange, yellow, and red. Temperatures start to cool mid to late October, with fall temperatures ranging between 44°F (7°C) and 64°F (17.5°C).

Festivals & events in October

  • Chicago International Film Festival
  • Chicago Marathon
  • Chicago Beer Fest


Although winter is beginning to set in, if you enjoy cool temperatures, early November is a great time to visit Chicago, as attractions are less crowded. The weather can be unpredictable, though, with some snow towards the end of the month.

Marina City in November

Temperatures range from 33°F (1°C) at night to 48°F (9°C) during the day, with around just four hours of sunshine a day. The city becomes busier towards the middle of November when people start preparing for Thanksgiving.

Preparing for the holiday season, November is a festive time of year in the city. Join over a million spectators under a million lights in the Magnificent Mile during the Magnificent Mile Lights Festival, or get in the festive spirit at the Chicago Thanksgiving Parade in the Chicago Loop.

Festivals & events in November

  • The Magnificent Mile Lights Festival
  • Christmas Tree Lighting Ceremony
  • Chicago Thanksgiving Parade
  • Chicago Comic and Entertainment Expo


December in Chicago is cold and grey but full of festive cheer! Temperatures during the day range average around 35°F (2 °C), while nights see the mercury dipping below zero to 22°F (-6°C).

Downtown Ice Rink in December

Days are short in December. With the winter solstice falling on the 21 December, you’ll only see about 3.5 hours of sunshine a day on average by the middle of the month. Nonetheless, the city is alive with people shopping for Christmas and getting ready for the new year.

Festivals & events in December

  • Christkindlmarket Chicago
  • ZooLights at Lincoln Park Zoo
  • Chicago Wine Fest
  • The Winterfest Wonderfest
  • New Year’s Eve Blast

Ryan O'Rourke is a seasoned traveler and the founder & editor of Treksplorer, a fiercely independent guide to mid-range luxury travel for busy people. With over 20 years of extensive travel experience, Ryan has journeyed through over 50 countries, uncovering hidden gems and sharing firsthand, unsponsored insights on what to see & do and where to eat, drink & stay. Backed by his travel experience and in-depth research, Ryan’s travel advice and writing has been featured in publications like the Huffington Post and Matador Network. You can connect with Ryan on Twitter/X at @rtorourke.

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